Enhanced antiamyloidal activity of hydroxy cinnamic acids by enzymatic esterification with alkyl alcohols
Abstract Lipophilic derivatives of hydroxyl cinnamic acids ( HCA s) including caffeic acid ( CA ), ferulic acid, sinapic acid ( SA ), and chlorogenic acid were synthesized by esterification with butanol, octanol, or hexadecanol catalyzed by the lipase from C andida antarctica to investigate the effe...
| Published in: | Biotechnology and Applied Biochemistry |
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| Main Authors: | , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2014
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/bab.1182 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fbab.1182 https://iubmb.onlinelibrary.wiley.com/doi/pdf/10.1002/bab.1182 |
| Summary: | Abstract Lipophilic derivatives of hydroxyl cinnamic acids ( HCA s) including caffeic acid ( CA ), ferulic acid, sinapic acid ( SA ), and chlorogenic acid were synthesized by esterification with butanol, octanol, or hexadecanol catalyzed by the lipase from C andida antarctica to investigate the effect of lipophilicity on their antiamyloidal activity assessed by the inhibitory activities toward fibrillization of amyloid β ( A β) peptide. Among them, CA showed the highest activity at 50 μM, reducing the amyloid fibril formation of A β to 34.4 ± 6.8%. The antiamyloidal effects of HCA s were enhanced by esterification with alkyl alcohols, and the longer alkyl chain tended to be more effective except for SA. A β fibril formation was suppressed by the hexadecyl ester of CA, which was reduced to 8.8 ± 2.3%. In contrast, those of octyl and butyl esters were 19.3 ± 2.3% and 41.6 ± 6.1%, respectively. These results show that lipophilicity plays an important role in the antiamyloidal activities of esterified phenolic compounds. |
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